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    1. City = Windermere
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    9508 Windy Ridge Road
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    Details for 9508 Windy Ridge Road, WINDERMERE, FL 34786
    Single Family
    1. Price: $30,000,000.00
    2. Price sqft: $639.85 / sqft
    3. Days On Market: 52
    4. Bedrooms: 7
    5. Baths: 14
    6. Garage / Parking Spaces: 12
    7. Bldg sqft: 46886
    8. Acreage: 18.16 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: Yes
    12. Wateraccess: Yes
    13. Waterfront Type: Lake Front,Lake Privileges
    14. Year Built: 2011
    MLS#: O6388674
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Elementary School: Thornebrooke Elem
    5. Middle School: Gotha
    6. High School: Olympia
    7. Provided by: DOUGLAS ELLIMAN
    8. mfrmls
    9. DMCA Notice
    Presenting Windy Ridge Estate on 18 gated acres with 614 feet of pristine frontage on Lake Down, Butler Chain of Lakes. Manicured grounds, panoramic water views, and over 50,000 SF across multiple str
    Listing Details and 40 Additional Pictures
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    11900 Lake Butler Boulevard
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    Details for 11900 Lake Butler Boulevard, WINDERMERE, FL 34786
    Single Family
    1. Price: $17,250,000.00
    2. Price sqft: $758.98 / sqft
    3. Previous Price: $18,500,000
    4. Last Price Change: 04/16/26
    5. Days On Market: 419
    6. Bedrooms: 7
    7. Baths: 9
    8. Garage / Parking Spaces: 6
    9. Bldg sqft: 22728
    10. Acreage: 3.75 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Lake Front,Lake Privileges
    16. Year Built: 2014
    MLS#: O6275556
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Metcalf Park Rep
    5. Elementary School: Windermere Elem
    6. Middle School: Chain of Lakes
    7. High School: Olympia
    8. Provided by: STOCKWORTH REALTY GROUP
    9. mfrmls
    10. DMCA Notice
    Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermeres largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 f
    Listing Details and 90 Additional Pictures
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    12488 Park Avenue
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    Details for 12488 Park Avenue, WINDERMERE, FL 34786
    Single Family
    1. Price: $15,500,000.00
    2. Price sqft: $878.09 / sqft
    3. Days On Market: 23
    4. Bedrooms: 10
    5. Baths: 17
    6. Garage / Parking Spaces: 9
    7. Bldg sqft: 17652
    8. Acreage: 2.75 acres
    9. Pool: Yes
    10. Spa/HotTub: Yes
    11. Waterfront: Yes
    12. Wateraccess: Yes
    13. Waterfront Type: Lake Privileges
    14. Year Built: 1996
    MLS#: O6395291
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Chaine Du Lac
    5. Elementary School: Windermere Elem
    6. Middle School: Bridgewater
    7. High School: Windermere
    8. Provided by: ONE LUXURY INTERNATIONAL LLC
    9. mfrmls
    10. DMCA Notice
    Commanding a rare 2.75 acre lakefront setting on the coveted Butler Chain of Lakes, this extraordinary Windermere estate is a true work of art. Recently completed after a meticulous, ground up transfo
    Listing Details and 67 Additional Pictures
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    9621 Windy Ridge Road
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    Details for 9621 Windy Ridge Road, WINDERMERE, FL 34786
    Single Family
    1. Price: $13,540,000.00
    2. Price sqft: $493.58 / sqft
    3. Previous Price: $13,550,000
    4. Last Price Change: 05/01/26
    5. Days On Market: 18
    6. Bedrooms: 9
    7. Baths: 16
    8. Garage / Parking Spaces: 8
    9. Bldg sqft: 27432
    10. Acreage: 2.50 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 2025
    MLS#: O6400740
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Windsor Hill
    5. Provided by: CITARELLI REALTY GROUP LLC
    6. mfrmls
    7. DMCA Notice
    Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protect
    Listing Details and 27 Additional Pictures
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    9323 Gladys Garden Court
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    Details for 9323 Gladys Garden Court, WINDERMERE, FL 34786
    Single Family
    1. Price: $12,500,000.00
    2. Price sqft: $999.20 / sqft
    3. Previous Price: $13,995,000
    4. Last Price Change: 04/04/26
    5. Days On Market: 84
    6. Bedrooms: 6
    7. Baths: 10
    8. Garage / Parking Spaces: 4
    9. Bldg sqft: 12510
    10. Acreage: 0.26 acres
    11. Pool: Yes
    12. Waterfront: No
    13. Year Built: 2026
    MLS#: O6381880
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Isleworth
    5. Elementary School: Windermere Elem
    6. Middle School: Chain of Lakes
    7. High School: Olympia
    8. Provided by: CORCORAN PREMIER REALTY
    9. mfrmls
    10. DMCA Notice
    Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury
    Listing Details and 83 Additional Pictures
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    6149 Grosvenor Shore Dr
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    Details for 6149 Grosvenor Shore Dr, WINDERMERE, FL 34786
    Single Family
    1. Price: $10,900,000.00
    2. Price sqft: $1,194.91 / sqft
    3. Previous Price: $9,999,000
    4. Last Price Change: 04/25/26
    5. Days On Market: 179
    6. Bedrooms: 6
    7. Baths: 8
    8. Garage / Parking Spaces: 7
    9. Bldg sqft: 9122
    10. Acreage: 2.65 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Lake Privileges
    16. Year Built: 2013
    MLS#: O6356355
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Keenes Pointe
    5. Elementary School: Windermere Elem
    6. Middle School: Bridgewater
    7. High School: Windermere
    8. Provided by: SOUTHERN REALTY GROUP LLC
    9. mfrmls
    10. DMCA Notice
    Keene's Pointe Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and me
    Listing Details and 74 Additional Pictures
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    4226 Downeast Lane
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    Details for 4226 Downeast Lane, WINDERMERE, FL 34786
    Land
    1. Price: $10,500,000.00
    2. Previous Price: $11,800,000
    3. Last Price Change: 04/09/26
    4. Days On Market: 143
    5. Acreage: 9.03 acres
    6. Pool: No
    7. Waterfront: Yes
    8. Wateraccess: Yes
    9. Waterfront Type: Lake Privileges
    10. Year Built: Not Available
    MLS#: O6367852
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Elementary School: Windermere Elem
    5. Middle School: Chain of Lakes
    6. High School: Olympia
    7. Provided by: COLDWELL BANKER RESIDENTIAL RE
    8. mfrmls
    9. DMCA Notice
    Dramatic price improvement. Exceptional development opportunity, currently r ce zoning should allow for 3 luxury home sites discover over 5+acres of waterfront land with 300 feet of pristine shoreline
    Listing Details and 27 Additional Pictures
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    4226 Downeast Lane
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    Details for 4226 Downeast Lane, WINDERMERE, FL 34786
    Single Family
    1. Price: $10,500,000.00
    2. Price sqft: $1,232.97 / sqft
    3. Previous Price: $11,800,000
    4. Last Price Change: 04/09/26
    5. Days On Market: 196
    6. Bedrooms: 5
    7. Baths: 3
    8. Garage / Parking Spaces: 4
    9. Bldg sqft: 8516
    10. Acreage: 9.03 acres
    11. Pool: Yes
    12. Waterfront: Yes
    13. Wateraccess: Yes
    14. Waterfront Type: Lake Front
    15. Year Built: 1980
    MLS#: O6355233
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Elementary School: Windermere Elem
    5. Middle School: Chain of Lakes
    6. High School: Olympia
    7. Provided by: COLDWELL BANKER RESIDENTIAL RE
    8. mfrmls
    9. DMCA Notice
    Dramatic price improvement. Exceptional development opportunity, currently r ce zoning should allow for 3 luxury home sites discover over 5+acres of waterfront land with 300 feet of pristine shorelin
    Listing Details and 28 Additional Pictures
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    6137 Grosvenor Shore Drive
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    Details for 6137 Grosvenor Shore Drive, WINDERMERE, FL 34786
    Single Family
    1. Price: $8,495,000.00
    2. Price sqft: $568.84 / sqft
    3. Previous Price: $8,995,000
    4. Last Price Change: 04/29/26
    5. Days On Market: 400
    6. Bedrooms: 6
    7. Baths: 9
    8. Garage / Parking Spaces: 5
    9. Bldg sqft: 14934
    10. Acreage: 2.20 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Lake Privileges,Riparian Rights
    16. Year Built: 2010
    MLS#: O6294487
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Keenes Pointe
    5. Elementary School: Windermere Elem
    6. Middle School: Bridgewater
    7. High School: Windermere
    8. Provided by: PREMIER SOTHEBY'S INTL. REALTY
    9. mfrmls
    10. DMCA Notice
    Experience luxury lakefront living on a grand scale in this custom built Modern Mediterranean estate on Lake Tibet, part of the pristine Butler Chain of Lakes. The three story residence spans 9,571 sq
    Listing Details and 61 Additional Pictures
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    9343 Tibet Pointe Circle
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    Details for 9343 Tibet Pointe Circle, WINDERMERE, FL 34786
    Single Family
    1. Price: $7,950,000.00
    2. Price sqft: $704.79 / sqft
    3. Previous Price: $8,250,000
    4. Last Price Change: 12/22/25
    5. Days On Market: 511
    6. Bedrooms: 7
    7. Baths: 10
    8. Garage / Parking Spaces: 4
    9. Bldg sqft: 11280
    10. Acreage: 1.54 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Lake Privileges
    16. Year Built: 2004
    MLS#: O6264629
    1. County: ORANGE
    2. City: WINDERMERE
    3. Zipcode: 34786
    4. Subdivision: Keenes Pointe
    5. Provided by: LA ROSA REALTY LLC
    6. mfrmls
    7. DMCA Notice
    PRICE Improvenent!! Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completely updated. The modern exterior color brig
    Listing Details and 99 Additional Pictures
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    Equal Housing Opportunity
    Listings provided courtesy of The Hernando County Association of Realtors MLS.
    Listing Data ©2026 REALTOR® Association of Citrus County
    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
    Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
    Datafeed Last updated on May 9, 2026 @ 12:00 am
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